The dissertation provides an in-depth analysis of the phenomenon of modernist and avant-garde trends and directions in Ukraine's theatrical art of the first three decades of the 20th century - such as proto-expressionism, expressionism, futurism and constructivism. The study embraces a dramatic and contradictory period in the development of the Ukrainian theatrical art, a period that proved full of aesthetic searches and discoveries and was encompassing a certain "change of epochs", as well as reflecting the historic transition towards new categories in the arts thinking. The main focus in the dissertation is made on the primarily modernist and avant-garde searches of stage directors, scene designers and other practitioners of art. By contrast, in the past the theatrical process of that time was mostly studied in line with the ideological connotations of the Soviet period - that is without a deep aesthetic analysis and, as a matter of fact, ignoring any concepts of avant-garde art. Taking into consideration programmatic works by European philosophers and works belonging to representatives of the Kyiv philosophical school - such as M. Berdyaev, L. Shestov, O. Zakrzhevskyi - the dissertation employs a historical-philosophical analysis of the theatrical proto-expressionism. This has enabled the author to conclude that at its early stages the Ukrainian theatrical modernism had been highly ambivalent. Based on the general scientific methods and principles of analysis, such as historism, systematisation, generalisation and others, the dissertation is taking up the case of proto-expressionism to re-construct theatrical modernism in the-then Ukraine and trace its specifics, as well as the innovations in the area of art semantics. As a result of the study, the evolution of the theatrical avant-garde in Ukraine of the allotted period can be presented as a three-stage process, and the author finds and points to respective stage-by-stage distinctions. At that, avant-garde itself is being viewed as a complex of left-leaning art currents functioning in parallel with traditional, realism-directed perspectives in the development of the Ukrainian theatre. A considerable part of the dissertation is devoted to the analysis of art-works of such experimentalist directors as Les' Kurbas, Faust Lopatinsky, Mark Tereshchenko, Borys Glagolin, Ihor Terentiev. In respect of these directors, the author explores form-setting trends in their professional practices and finds out that such trends were essentially determined by aesthetics of expressionism, futurism and constructivism and proved fundamentally important in stimulating the birth of innovative concepts in question.